Composition containing burdock seed oil and production method thereof

Abstract

The purpose of the present invention is to produce and provide a composition containing burdock seed oil having excellent stability. The present invention relates to a composition containing (A) arctium lappa seed oil and (B) triethyl citrate and containing 1 to 7.5 mass% of arctigenin derived from component (A), and a method for producing the same.

Description

Technical Field

[0001] The present invention relates to a composition containing burdock seed oil and a method for producing the same. Background Art

[0002] As is well known, the fruits of Arctium lappa Linne (Compositae), which is a member of the Compositae family, contain arctiin, a lignin glycoside, and arctigenin, its aglycone. A method for producing an Arctium lappa fruit extract containing a high content of arctigenin from Arctium lappa fruits is known (Patent Document 1).

[0003] The stability of burdock seed oil, which is an extract of Arctium lappa fruits, has not been sufficiently studied.

[0004] Citation List

[0005] Patent Document

[0006] Patent Document 1: WO 2012 / 043549 A Summary of the Invention

[0007] Technical Problem

[0008] An object of the present invention is to produce and provide a composition containing burdock seed oil with excellent stability.

[0009] Solution to the Problem

[0010] The present inventors found that a composition containing (A) burdock seed oil and (B) an ester compound or an ethylene glycol ether is stable. Thus, the present invention has been completed.

[0011] The present invention provides a composition containing burdock seed oil with excellent stability. In addition, the present invention provides a method for producing a composition containing burdock seed oil with excellent stability.

[0012] That is, the present invention relates to a composition containing (A) burdock seed oil and (B) an ester compound or an ethylene glycol ether.

[0013] Preferred aspects of the present invention are as follows:

[0014] [1] A composition containing (A) burdock seed oil and (B) one or more compounds selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol;

[0015] [2] The composition according to [1], wherein the content of arctigenin derived from the component (A) is 1 to 7.5% by mass;

[0016] [3] The composition according to [1] or [2], wherein the content of arctigenin derived from the component (A) is 2 to 15% by mass based on the total amount of the component (A);

[0017] [4] The composition according to any one of [1] to [3], wherein the content of one or more compounds of (B) selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol is 10 to 90% by mass;

[0018] [5] A method for producing a composition, which includes a step of blending (A) burdock seed oil and (B) one or more compounds selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol;

[0019] [6] The method for producing a composition according to [5], which includes a step of blending the component (A) such that the content of arctigenin derived from the component (A) is 1 to 7.5% by mass;

[0020] [7] The method for producing a composition according to [5] or [6], wherein based on the total amount of the component (A), the content of arctigenin derived from the component (A) is 2 to 15% by mass;

[0021] [8] The method for producing a composition according to any one of [5] to [7], wherein the content of one or more compounds of (B) selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol is 10 to 90% by mass;

[0022] [9] A method for producing a composition, which includes a step of blending (A) burdock seed oil and (B) one or more compounds selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol, wherein highly concentrated arctigenin is contained in the burdock seed oil;

[0023]

[10] An external preparation or oral preparation containing the composition according to [1] to [4], wherein the burdock seed oil is the active ingredient;

[0024]

[11] An external preparation or oral preparation containing the composition according to [2] or [3], wherein arctigenin is the active ingredient;

[0025]

[12] The composition according to any one of [1] to [4], wherein the composition is substantially free of arctiin derived from the burdock seed oil (A);

[0026]

[13] The method for producing a composition according to any one of [5] to [9], wherein the composition is substantially free of arctiin derived from the burdock seed oil (A); and

[0027]

[14] The external or oral preparation according to

[10] or

[11] , wherein the preparation is substantially free of arctiin derived from the burdock seed oil (A).

[0028] Advantages of the invention

[0029] The composition containing burdock seeds of the present invention contains (A) burdock seed oil and (B) an ester compound or ethylene glycol ether, and thus has excellent stability. Detailed description of the specific implementation

[0030] Hereinafter, examples for implementing the present invention will be described in detail. However, the present invention is not limited to the following examples.

[0031] [1. Composition]

[0032] The composition of the present invention is a composition containing (A) burdock seed oil and (B) an ester compound or ethylene glycol ether, and the content of arctigenin derived from component (A) is preferably 1 to 7.5% by mass.

[0033] For example, the composition according to one embodiment is a composition containing (A) burdock seed oil and (B) one or more compounds selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol, and the content of arctigenin derived from component (A) is 1 to 7.5% by mass.

[0034] [Component (A)]

[0035] The burdock seed oil is not particularly limited as long as the oil is obtained from the seeds of Arctum lappa Linne (Compositae). The oil can preferably be obtained by extracting from burdock seeds. For example, the burdock seed oil can be produced and obtained by the following method, or commercially available burdock seed oil can be used. One can be used alone, or two or more can be used in combination.

[0036] The content of component (A) in the composition according to this embodiment is not particularly limited, and is appropriately set according to the type and content of other components to be blended, the use and dosage form of the composition, etc. Regarding the content of component (A), from the viewpoint of more significantly exerting the effects of the present invention, based on the total amount of the composition, the total content of component (A) can be, for example, 10 to 90% by mass, 20 to 80% by mass, preferably 30 to 70% by mass, more preferably 35 to 65% by mass, still more preferably 40 to 60% by mass, even more preferably 45 to 60% by mass, and particularly preferably 45 to 55% by mass.

[0037] The composition according to this embodiment contains arctigenin. The content of arctigenin is not particularly limited and is appropriately set according to the types and contents of other components to be blended, the use and dosage form of the composition, and the like. Regarding the content of arctigenin, from the viewpoint of more significantly exerting the effects of the present invention, based on the total amount of the composition, the total content of arctigenin may be, for example, 1 to 7.5% by mass, 1 to 6% by mass, preferably 1 to 5.5% by mass, more preferably 1 to 5% by mass, still more preferably 1.5 to 4.5% by mass, even more preferably 2 to 4% by mass, and particularly preferably 2.5 to 3.5% by mass.

[0038] The composition according to this embodiment contains arctigenin derived from component (A). Regarding the content of arctigenin derived from component (A), from the viewpoint of more significantly exerting the effects of the present invention, based on the total amount of component (A), the total content of arctigenin derived from component (A) may be, for example, 2 to 15% by mass, 2 to 12% by mass, preferably 2 to 11% by mass, more preferably 2 to 10% by mass, still more preferably 3 to 9% by mass, even more preferably 4 to 8% by mass, and particularly preferably 5 to 7% by mass. The content of arctigenin derived from component (A) is not particularly limited and is appropriately set according to the types and contents of other components to be blended, the use and dosage form of the composition, and the like.

[0039] <Component (B)>

[0040] From the viewpoint of more significantly exerting the effects of the present invention, component (B) is preferably an ester compound or a glycol ether, more preferably a C 10-30 ester or a C 4-15 glycol ether, and still more preferably a C 12-27 ester or a C 4-8 glycol ether. Even more preferably, it is a C 12-27 triester (for example, triethyl citrate ((C 12 )) or glyceryl tri(ethylhexanoate) ((C 27 ))); a C 12-14 diester (for example, isopropyl adipate ((C 12 )) or diethyl sebacate ((C 14 ))); or a C 4-8 glycol ether (for example, butanediol ((C 4 )) or diethylene glycol monoethyl ether (ethoxydiglycol) ((C 6 )) or methoxymethylbutanol ((C 6 )) or (C 8Ethylene glycol monophenyl ether (phenoxyethanol)). Component (B) has fluidity to allow stirring and mixing with component (A) at 20 to 80 °C. As component (B), commercially available products can be used. One type of component (B) can be used alone, or two or more types thereof can be used in combination. There is no particular limitation on component (B) as long as it is used in a known manner. Examples of component (B) include, but are not limited to, one or more compounds selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol. Alternatively, triethyl citrate can be contained alone. Triethyl citrate can be contained at least, and one or more compounds selected from the group consisting of diisopropyl adipate, diethyl sebacate, and phenoxyethanol can be further contained.

[0041] The content of component (B) in the composition according to this example is not particularly limited, and is appropriately set according to the type of component (B), the types and contents of other components to be blended, the use and dosage form of the composition, etc. Regarding the content of component (B), from the viewpoint of more significantly exerting the effects of the present invention, based on the total amount of the composition, the total content of component (B) can be, for example, 10 to 90% by mass, 20 to 80% by mass, preferably 30 to 70% by mass, more preferably 35 to 65% by mass, still more preferably 40 to 60% by mass, even more preferably 45 to 60% by mass, and particularly preferably 45 to 55% by mass.

[0042] (Other components)

[0043] In addition to components (A) and (B), other components can be further added to the composition according to this example.

[0044] Preferably, the composition according to this example does not contain or substantially does not contain arctiin. Here, "substantially does not contain" means that the amount of arctiin in the composition is 0.01% by mass or less, preferably 0.001% by mass or less, and more preferably 0.0001% by mass or less.

[0045] [2. Method for producing the composition]

[0046] Component (A) contained in the composition according to this example can be produced through steps such as crushing burdock seeds, subjecting burdock seeds to extraction to obtain burdock seed oil, filtering the burdock seed oil, including a step of highly concentrating arctigenin in the burdock seed oil, a concentration step, a solid-liquid separation step, etc. From the viewpoint of more significantly exerting the effects of the present invention, if appropriate, each step can be set, and it is not necessary to include all steps.

[0047] [Step of crushing burdock seeds]

[0048] Burdock seeds can be crushed by known means, and commercially available crushers can also be used. Commercially available burdock seeds crushed to any size (particle size) can be used. From the viewpoint of more significantly exerting the effects of the present invention, the arctigenin content of the burdock seeds can be measured, and then the burdock seeds suitable for the present invention can be selected.

[0049] <Subject the burdock seeds to an extraction step to obtain burdock seed oil>

[0050] The crushed burdock seeds and a solvent can be mixed and extracted under conditions from room temperature to high temperature to obtain burdock seed oil. In the extraction step, water or an organic solvent (e.g., methanol, ethanol, propanol, acetone, oil) or a mixture thereof can be used, and the yield of arctigenin can be increased by preferably selecting a solvent having good compatibility with arctigenin. The solvent used can be a commercially available solvent. The extraction treatment used can be any known extraction process, such as heating and stirring, heating and refluxing, drip extraction, soaking extraction, or pressure extraction. The temperature of the extraction treatment can be any temperature, but from the viewpoint of more significantly exerting the effects of the present invention, it can be 35°C or higher, 40°C or higher, 50°C or higher, 55°C or higher, 60°C or higher, or 65°C or higher. The temperature can also be 95°C or lower, 90°C or lower, 85°C or lower, 80°C or lower, or 75°C or lower. Although not limited, for example, 40 to 90°C is preferred, 55 to 90°C is more preferred, 60 to 85°C is even more preferred, and 65 to 80°C is even more preferred. The time for performing the extraction treatment is not limited, but preferably it is 30 minutes or longer, more preferably 35 minutes to 24 hours, even more preferably 45 minutes to 20 hours, and even more preferably 1 hour to 20 hours.

[0051] <Filter the burdock seed oil step>

[0052] In order to remove unnecessary components from the extracted burdock seed oil, filtration can be performed as needed. In order to determine the necessity of the filtration step, the components contained in the burdock seed oil can be analyzed and measured in advance. Filtration can be performed using known methods such as gel filtration, gel chromatography, thin layer chromatography, or filters and / or known devices.

[0053] <Include highly concentrated arctigenin in the burdock seed oil step>

[0054] In order to include a high concentration of arctigenin in the burdock seed oil, it is preferable to convert the arctiin contained in the burdock seed oil into arctigenin. Specifically, processes such as hydrolysis treatment, enzyme treatment, or reflux treatment can be performed, but are not limited thereto. From the viewpoint of more significantly exerting the effects of the present invention, hydrolysis treatment is preferred. The hydrolysis treatment can be promoted by, but not limited to, adding an acid. The acid used at this time is preferably a strong acid, and for example, hydrochloric acid, nitric acid, or sulfuric acid can be used.

[0055] The reaction temperature in this step is 40 °C or higher, 50 °C or higher, 60 °C or higher, or 65 °C or higher, and may be 90 °C or lower, 85 °C or lower, 80 °C or lower, or 75 °C or lower. For example, 40 to 90 °C is preferred, 50 to 85 °C is more preferred, 60 to 80 °C is even more preferred, and 65 to 75 °C is even more preferred. The reaction time is not limited, but is preferably 30 minutes or longer, more preferably 35 minutes to 24 hours, even more preferably 45 minutes to 20 hours, and even more preferably 1 hour to 20 hours.

[0056] <Concentration step>

[0057] Known concentration processes can be used to remove the solvent contained in the extracted burdock seed oil. Enrichment is preferably carried out to a concentration that exerts the effects of the present invention.

[0058] <Solid-liquid separation step>

[0059] To separate the extraction residue from the extracted burdock seed oil, known solid-liquid separation processes such as filtration, precipitation, and centrifugation can be carried out.

[0060] <Step of mixing component (A) and component (B) to obtain a composition>

[0061] The extracted burdock seed oil can be analyzed and measured by known methods to check the content of arctigenin. Component (A), component (B), and appropriate other components can be mixed to obtain the composition of the present invention. In the production of the composition, although not limited, it is preferably stirred and mixed at a temperature of, for example, 20 °C to 80 °C, preferably 20 °C to 60 °C, and more preferably 20 °C to 40 °C. The time for stirring and mixing is not limited, but can be 10 minutes to 10 hours, and preferably about 20 minutes to 5 hours. Here, the ratio between component (A) and component (B) is not limited, but based on 1 part by mass of component (A), component (B) is preferably about 0.1 to 10 parts by mass, and more preferably 0.5 to 5 parts by mass. After mixing component (A) and component (B), analysis and measurement can be carried out by known methods to check the content of arctigenin. Here, the ratio between component (A) and component (B) is not limited, but based on 1 part by mass of component (A), component (B) is preferably about 0.1 to 10 parts by mass, more preferably 0.5 to 5 parts by mass, and even more preferably 0.5 to 1.5 parts by mass.

[0062] [3. External preparation or oral preparation]

[0063] The composition according to this embodiment can be an external preparation or an oral preparation. An external preparation or an oral preparation containing the composition according to this embodiment can be prepared. An external preparation means a form applied to the outer surface of a living body. An oral preparation means a form in which the oral preparation is ingested into the body from the oral cavity of the living body and administered.

[0064] In addition to components (A) and (B), the composition according to this embodiment or an external preparation containing the composition according to this embodiment can further contain one or two or more components, such as a whitening component, an anti-inflammatory component, an antibacterial component, a cell activation component, an astringent component, an antioxidant component, an anti-aging component, or a moisturizing component, as long as the effects of the present invention are not impaired. Each of these components is not particularly limited as long as the component is generally used as a component of an external preparation for the skin in the fields of pharmaceuticals, quasi-drugs, or cosmetics, or can be used in the future, and any component can be appropriately selected and used.

[0065] As long as the effects of the present invention are not impaired, in addition to components (A) and (B), the composition according to this embodiment or an oral preparation containing the composition according to this embodiment can also contain a pharmacologically active ingredient or a physiologically active ingredient. A pharmacologically active ingredient or a physiologically active ingredient can be used alone, or two or more of them can be used in combination. In addition, the oral preparation can contain additives such as excipients, binders, disintegrants, lubricants, coloring agents, taste masking agents, odor masking agents, sugars, sugar alcohols / polyhydric alcohols, high-intensity sweeteners, fats and oils, emulsifiers, thickeners, acidifying agents, and fruit juices.

[0066] The external preparation or the oral preparation can be used in the form of a drug, a cosmetic, or a food. As long as the effects of the present invention are not impaired, a known base or carrier can be mixed therewith to prepare the external preparation or the oral preparation. Examples of known forms include: liquids, suspensions, emulsions, creams, ointments, gels, liniments, lotions, aerosols, foams, powders, patches, sheets in which a non-woven fabric is impregnated with a drug solution, sticks such as lipsticks, jellies, syrups, granules, lozenges, chewable tablets, pills, tablets, and capsules.

[0067] [Method for producing an external preparation or an oral preparation]

[0068] In one embodiment of the present invention, a method for producing an external preparation or an oral preparation can also be provided. The content of each component and other conditions are consistent with those described in [1. Composition], [2. Method for producing a composition], and [3. External preparation or oral preparation].

[0069] Examples

[0070] Hereinafter, the present invention will be specifically described based on test examples, but the present invention is not limited thereto. In addition, the blending amounts in the following examples, etc. are expressed in mass%.

[0071] [Production Example 1]

[0072] The ground and pulverized burdock seeds were charged into a sufficient amount of 98% aqueous ethanol solution and stirred at 40 °C for 18 hours. The resulting liquid was allowed to stand at room temperature to precipitate the residue of the burdock seeds. The supernatant was collected to obtain burdock seed oil (the step of subjecting the burdock seeds to extraction to obtain burdock seed oil). Filtration was carried out using a pad of silica gel and diatomaceous earth with a blending ratio of 2:1.

[0073] The amounts of arctigenin and arctiin contained in the obtained burdock seed oil were measured by high performance liquid chromatography. As a result, the amount of arctigenin was 1.1% by mass, and the amount of arctiin was 19.3% by mass (the step of filtering the burdock seed oil). Sulfuric acid was added to the recovered burdock seed oil, and the resulting mixture was stirred at 70 °C for 18 hours for hydrolysis treatment. The pH of the burdock seed oil was adjusted to about 5.5 with a pH regulator. Decolorizing carbon was added to the burdock seed oil, and the mixture was stirred for 18 hours. Thereafter, filtration was carried out using a pad made of diatomaceous earth, and the filtered liquid was washed with ethanol (the step of containing highly concentrated arctigenin in the burdock seed oil). The burdock seed oil was concentrated using a rotary evaporator (at 30 °C), and it was allowed to stand in an oven for 12 hours (at 22 °C) to precipitate the residue of the burdock seed oil. The separated oil phase was separated from the solid phase and dried overnight in a vacuum oven (the concentration step, the solid-liquid separation step). The amounts of arctigenin and arctiin contained in the obtained burdock seed oil were measured by high performance liquid chromatography. As a result, the amount of arctigenin was 5.4% by mass, and arctiin was not detected.

[0074] [Examples and Comparative Examples]

[0075] As shown in Table 2, the burdock seed oil (A) and component (B) obtained in Production Example 1 were weighed and placed in a cylindrical beaker made of polyethylene. Component (A) and component (B) were stirred and mixed at room temperature for 30 minutes to prepare each composition of the example. Only the burdock seed oil (A) obtained in Production Example 1 was used as the composition of the comparative example. Note that component (B) in the table means that all components are 100% of each indicated component.

[0076] [Test Example 1]

[0077] As shown in Table 1, weigh the burdock seed oil (A) and component (B) obtained in Production Example 1, and place them in a glass beaker. Stir and mix component (A) and component (B) at room temperature for 30 minutes, and then transfer them to a cylindrical container made of polyethylene terephthalate. Seal the container by closing the screw cap. After allowing each composition to stand at 4°C for 1 week, observe the appearance stability of the composition. When observing the bottom surface vicinity from the side of the container, a test liquid without precipitation is evaluated as ◎, a test liquid with slight precipitation is evaluated as ○, and a test liquid with precipitation and color gradation (non-uniformity) is evaluated as ×. The results are shown in Table 1.

[0078] [Table 1]

[0079] (mass%)

[0080] Component Name Comparative Example 1-1 Example 1-1 Example 1-2 Example 1-3 Example 1-4 (A) Arctium lappa seed oil (Production Example 1) 100 50 50 50 50 (B) Triethyl citrate - 50 - - - (B) Diisopropyl adipate - - 50 - - (B) Diethyl sebacate - - - 50 - (B) Phenoxyethanol - - - - 50 Total amount 100 100 100 100 100 Stability × ◎ ○ ○ ◎

[0081] As shown in Table 1, the composition containing only burdock seed oil (Production Example 1) (Comparative Example 1-1) has low stability after being allowed to stand at 4°C for 1 week. It was found that the compositions containing burdock seed oil (Production Example 1) and component (B) (Examples 1-1 to 1-4) are highly stable.

[0082] [Test Example 2]

[0083] After preparing each composition, then allow it to stand for 5 minutes and observe the appearance stability of the composition. When observing the composition from the side of the beaker, a test liquid in which no area showing color gradation (non-uniformity) occurs is evaluated as ◎, a test liquid in which the area showing color gradation is less than 50% is evaluated as ○, a test liquid in which the area showing color gradation is 50% or more but no separation between component (A) and component (B) is observed is evaluated as Δ, and a test liquid in which separation between component (A) and component (B) is observed is evaluated as ×.

[0084] Even when no area showing color gradation is observed, a test liquid in which separation between component (A) and component (B) is observed is evaluated as ×. The results are shown in Table 2.

[0085] [Table 2]

[0086] (mass%)

[0087] Component Name Example 2-1 Example 2-2 Example 2-3 Example 2-4 Example 2-5 Example 2-6 Example 2-7 (A) Arctium lappa seed oil (Production Example 1) 50 50 50 50 50 50 50 (B) Triethyl citrate 50 - - - - - - (B) Glycerol tri(2-ethylhexanoate) - 50 - - - - - (B) Diisopropyl adipate - - 50 - - - - (B) Diethyl sebacate - - - 50 - - - (B) Diethoxyethyl succinate - - - - 50 - - (B) Phenoxyethanol - - - - - 50 - (B) 1,3-Butanediol - - - - - - 50 Total amount 100 100 100 100 100 100 100 Stability ◎ △ ○ ○ △ ◎ △

[0088] [Test Example 3]

[0089] First, weigh 50 g of Example 2-1 and place it in a polypropylene container, and seal the container by closing the screw cap (the filling rate of the test liquid in the container is 90%). Allow the composition to stand at 60 °C for 2 weeks (heat treatment).

[0090] Measure the arctigenin content of Example 2-1 after heat treatment by high performance liquid chromatography. Perform the same test on Example 2-6. The results are shown in Table 3.

[0091] [Table 3]

[0092] (mass%)

[0093]

[0094] As shown in Table 3, after heat treatment of the composition containing burdock seed oil and triethyl citrate (Example 2-1), the arctigenin content is 2.7 mass%. This means that based on the total amount of burdock seed oil (A), the content of arctigenin derived from component (A) is 5.4 mass%. From the fact that burdock seed oil containing 5.4 mass% arctigenin was produced in Production Example 1, it has been revealed that the content of arctigenin in the composition of the present invention does not change due to heat treatment, and thus the composition is highly stable. Also in the test liquid containing phenoxyethanol as component (B) (Example 2-6), the stability of arctigenin was found to be as high as in Example 2-1.

Claims

1. A composition, comprising: (A) Arctium lappa seed oil; and (B) triethyl citrate, wherein the content of arctigenin derived from the component (A) is 1 to 7.5% by mass.

2. The composition according to claim 1, wherein the content of (B) triethyl citrate is 10 to 90% by mass.

3. A method for producing a composition, comprising blending (A) Arctium lappa seed oil and (B) triethyl citrate, wherein the component (A) is blended such that the arctigenin derived from the component (A) is 1 to 7.5% by mass.

4. A method for producing a composition, comprising the step of blending (A) Arctium lappa seed oil and (B) one or more compounds selected from the group consisting of triethyl citrate, diisopropyl adipate, diethyl sebacate, and phenoxyethanol, wherein highly concentrated arctigenin is contained in the Arctium lappa seed oil.

5. The method for producing a composition according to claim 3 or 4, comprising the step of blending such that the content of (B) triethyl citrate is 10 to 90% by mass.

6. A method for producing an external preparation or an oral preparation, comprising the step of blending the composition according to claim 1 or 2.

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